


Pretty Blue Panties

by VanessaWolfie



Series: Kinktober 2018 [5]
Category: Teen Wolf (TV)
Genre: Alternate Universe - BDSM, Dom Lydia Martin, Dom Stiles Stilinski, F/M, Feet, Feminization, Large Cock, M/M, Panties, Small Penis, Sub Jackson Whittemore, Underage - Freeform, Verbal Humiliation, everybody the same age, sissification
Language: English
Status: Completed
Published: 2018-10-05
Updated: 2018-10-05
Packaged: 2019-07-25 14:09:24
Rating: Mature
Warnings: Underage
Chapters: 1
Words: 1,069
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16199102
Author URL: https://archiveofourown.org/users/VanessaWolfie/pseuds/VanessaWolfie
Summary: Lydia invites Stiles over to cuckold Jackson. Before he fucks her, he takes a moment to discuss it all with Lydia and then a moment to humiliate Jackson.This does not include Stiles actually fucking Lydia, that will be a later installation. Mostly dialogue about Jackson's huge humiliation kink. Over his little junk.





	Pretty Blue Panties

**Author's Note:**

> This is something that happens before Never Before Me, because here, they are still in high school, probably juniors and Lydia and Jackson are in a relationship. Stiles is single, just there for the night and the kink. 
> 
> There will hopefully be a whole series of installations into this 'verse, but as kind of implied in this one, this is an alternative universe with whole other rules about teenage/underage sex and BDSM. People are Doms or Subs or in rarer cases, neither. There is no timeframe or public announcement of your dynamic, but rather do you just slowly come into your own, however that is. 
> 
> 5\. **Feet** | Sadism/Masochism | Feederism | Shotgunning

“So, I go in there and what, humiliate him?” Stiles asks, point blank and honest. He’s trying to get a read on this situation, but honestly, he’s just kind of excited. He’s going to get to have sex with Lydia, who’s Jackson’s Domme, but also … very hot and Stiles isn’t quite sure she’s that dominant, because she hasn’t been making much of an impression on him. 

 

“Yes, he’s small, you know,  _ there _ and he likes to be belittled for it, degraded, it gets him going. I just try to give him what he needs, you know, and we’ve been talking about this for a while, cucking and well, … I …” and then she stops, and slides a palm over her face and Stiles gets the feeling that she’s way in over her head. And he gets that; they’re all a bit young, even if they all need these kind of things, because of their dynamics, but he’s still not sure he’s ever met a dominant that’s sounded quite that … desperate to fit the role before. It adds to his suspicions, but still, he’s not here to do anything about that. No matter what kinks they might have in their arsenal, he won’t even consider trying to get someone to cheat, not when they’re in a committed Domme/sub relationship. No, no way. 

 

“I want you to go and talk with him before I join you guys, just … degrade him, however feels most natural to you, just don’t, don’t share your cock with him, I want that to be mine for the night. It’s important that you mention that you are going to fuck me like he never could, and then reiterate that when you fuck me, as he watches. 

 

Other than that, feel free to add your own flare to it a little and uh, don’t be scared you’ll cross a line with the humiliation. I still haven’t found a line.” Lydia finally continues, stopping Stiles’s thought process.  

 

That also feels weird, both that she’d admit to not having found a limit with her sub, and that she’s basically giving him a ‘carte blanche. With her own sub. Anyway. Stiles is just here to enjoy some kinky sex. 

 

“Okay, got it. Any names or things he doesn’t want to be called? Or something he does want to be called?” 

 

Lydia thinks it over, but then says, with a sly smile on her face. “Nothing he doesn’t like to be called, but he likes being feminized, it all comes back to his size, you know?” 

 

Stiles really doesn’t, because a) he hasn’t seen Jackson’s little cock yet and b) it’s not like it’s a reality of his own. Still, he just nods and goes inside. 

 

There in the room, Jackson is standing and he’s wearing blue panties and he looks so different from school that Stiles almost does a double take. 

 

He’s in control though and he can feel the shift from when he was out having a conversation with Lydia, to this, now, where he’s in charge of Jackson, however brief and limited. 

 

He does a slow once over of Jackson’s whole body, making sure Jackson notices and he feels a gut curling giddiness when he sees Jackson flush. 

 

“Nice panties,  _ sissy. _ ” 

 

Jackson shivers and makes to cover himself with his hands, however pointless. 

 

“What are you trying to cover up there, huh, Jackson? I think the panties do a nice enough job of that, it’s not like your stuffing them with anything anyway.” 

 

“Put your hands flat on your ass, keep them there.” Stiles instructs, before stepping right up to him. He moves slowly but surely and plucks at the front of Jackson’s panties and pulls them down. “Yeah, not hiding an awful lot in there, are you? No wonder Lydia wanted me over here, she’s not getting fucked by you, that’s for sure. That thing is pretty much useless, isn’t it? Do you have a useless little cocklet Jackson?” 

 

Jackson isn’t looking him in the eye anymore, but he nods. 

 

“You better use your words here Jackson, or I might not let you watch me fuck your girlfriend like she wants to be fucked. She’ll be here, moaning in satisfaction, as I fuck her hard and good and you will just be somewhere else, in your pretty blue panties, alone.” 

 

“I have a useless little cocklet and I can’t fuck my mistress. Please, fuck my mistress in front of me. Show me how a man fucks.” 

Damn if that doesn’t do it for Stiles. Not exactly the ego boost part, but how Jackson just degraded himself, all for Stiles. Well, technically all for Lydia, but she’s not here and Jackson is definitely getting hard, just from all the talking. It’s a rush. Stiles might actually need to get a sub of his own, if it’s this awesome. 

 

“Now, that wasn’t so hard was it. Now, cover up that thing again. It’s getting hard, which is pretty useless, since you won’t do anything with it, so I think you should just hide it in those panties again, don’t you think.” 

 

“Yes sir,” is all Jackson says, as he rights the panties waistband again. 

 

“I think that since I’m going to do you this favor, of showing you how a real man fucks, you should thank me. Get down on your knees and kiss my feet. Five kisses on each foot, you don’t get anymore, and between each one, thank me personally and each time specify something I’ve done for you, or will do for you tonight.” 

 

He’d thought about that one and from what Lydia said and what Jackson himself both said and showed, he thought it’d be the best course of action. Give Jackson the time to degrade himself, but also put him in a humiliating situation, doing a humiliating thing. Stiles also just had a thing for people on their knees for him. Sue him. 

 

Jackson didn’t hesitate, he just knelt down, shifting close enough that it fit for him to bend over and kiss Stiles’s feet. 

 

“Thank you, sir, for putting me in my place.” *kiss* *kiss* “Thank you, sir, for pointing out my useless cocklet.” *kiss* “Thank you, sir, for letting me kiss your feet.” *kiss* and so it continued, with Jackson debasing himself further and further, until the last one *kiss* “Thank you, sir, for showing me how to fuck my mistress.” 

 

“Good sissygirl.” 

**Author's Note:**

> I will be going through the Kinktober prompt list pretty much like this, maybe not always on the right date, since I've got a big exam coming up on the tenth. If you like this please subscribe to my series, either the kinktober one, or if you like this 'verse of Stiles, Lydia and Jackson (and to be more people) then subscribe to that series. 
> 
> As always, comments are appricated, but the kudos button works wonders as well and mostly, I hope you enjoyed being here :)


End file.
